92326-42-6

Basic information

• Product Name: diheptan-4-ylidenehydrazine
• CAS NO: 92326-42-6
• Molecular Formula: C₁₄H₂₈N₂
• Molecular Weight: 224.3855
• Mol File: 92326-42-6.mol

Chemical Properties

• Boiling Point: 293.8°C at 760 mmHg
• Flash Point: 123.4°C
• Density: 0.85g/cm³
• Vapor Pressure: 0.00296mmHg at 25°C
• Refractive Index: 1.461
• CAS DataBase Reference: diheptan-4-ylidenehydrazine(CAS DataBase Reference)
• NIST Chemistry Reference: diheptan-4-ylidenehydrazine(92326-42-6)
• EPA Substance Registry System: diheptan-4-ylidenehydrazine(92326-42-6)

Safety Data

• Hazardous Substances Data: 92326-42-6(Hazardous Substances Data)

Upstream product

• 138723-85-0 2-methoxy-2-methyl-5,5-di-n-propyl-1,3,4-Δ³-oxadiazoline 
• 225659-86-9 dipropyldiazirine 

Downstream Products

• 16751-59-0 4-heptylamine 

Relevant articles and documents

Photolysis of dipropyldiazirine and trapping of dipropylcarbene with piperidine

Photolysis (350 nm) of dipropyldiazirine in methylene chloride at 4°C produces a mixture of E and Z 3-heptene in 81% yield in an E/Z ratio of 1.8. Tetrapropylazine was formed in less than 5% yield. Photolysis of dipropyldiazirine in the presence of piperidine leads to the formation of a carbene-amine adduct. In the presence of 0.06 M piperidine the yield of adduct is 48%, the yield of E and Z 3-heptene is 47% and the E/Z ratio of 3- heptenes is 1.1. The results show that heptene is formed by three pathways. One pathway involves dipropylcarbene formed directly from the diazirine, the other pathways are attributed to ionic and photochemical reactions of 4- diazoheptane and to the excited state of the diazirine precursor. Dipropylcarbene can be easily intercepted with a simple trap. The yield of this process is limited by the efficiency with which the precursor forms the carbene.

Chemistry and Kinetics of Dipropylcarbene in Solution

The photochemistry of 2-methoxy-2-methyl-5,5-dipropyl-Δ3-1,3,4-oxadiazoline (1a) and 2,2-dimethoxy-5,5-dipropyl-Δ3-1,3,4-oxadiazoline (1b) was investigated. Photolysis (300 nm) of these compounds in solution leads to fragmentation to 4-diazoheptane (major), which slowly forms the corresponding azine. Fragmentation to form 4-heptanone is also observed. Yields of 4-diazoheptane in CH2Cl2 are much larger than those in pentane. 4-Diazoheptane can be trapped with 1-pentene to form a pyrazoline or with methanol to form 4-methoxyheptane. The pyrazoline can be decomposed photochemically to form 1,1,2-tripropylcyclopropane. In solution, 4-diazoheptane is inefficiently photolyzed to dipropylcarbene (DPC), which can be trapped with piperidine or with pyridine in laser flash photolysis experiments. Analysis of the piperidine and pyridine data indicates that the lifetime of DPC in cyclohexane, methylene chloride, or Freon-113 (CF2ClCFCl2) solution at ambient temperature is controlled by 1,2 hydrogen migration to form Z- and E-3-heptene. The lifetime deduced under these conditions is ≈300 ps, which is about 20-fold shorter than that of dimethylcarbene in perfluorohexane at ambient temperature. Upon photolysis (254 nm) of oxadiazoline 1a in argon, 4-diazoheptane and 1-methoxydiazoethane are formed. These diazo compounds undergo subsequent photolysis that revealed the formation of methoxy(methyl)carbene and E- and Z-3-heptene. It was not possible to detect DPC in argon at 14 K.